SML1358

SGI-1027

≥98% (HPLC)

• Synonym(s): N-(4-(2-Amino-6-methylpyrimidin-4-ylamino)phenyl)-4-(quinolin-4-ylamino) benzamide
• Empirical Formula (Hill Notation): C₂₇H₂₃N₇O
• CAS Number: 1020149-73-8
• Molecular Weight: 461.52
• MDL number: MFCD27937047
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825813
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• color: white to light brown
• solubility: DMSO: 20 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: O=C(NC1=CC=C(NC2=NC(N)=NC(C)=C2)C=C1)C(C=C3)=CC=C3NC4=C(C=CC=C5)C5=NC=C4
• InChI: 1S/C27H23N7O/c1-17-16-25(34-27(28)30-17)32-20-10-12-21(13-11-20)33-26(35)18-6-8-19(9-7-18)31-24-14-15-29-23-5-3-2-4-22(23)24/h2-16H,1H3,(H,29,31)(H,33,35)(H3,28,30,32,34)
• InChI key: QSYLKMKIVWJAAK-UHFFFAOYSA-N

Description

Application

SGI-1027 has been used as a DNA methyltransferase inhibitor to study its effects on gene expression during osteogenic differentiation. It has also been used as a DNA methyltransferase 3a inhibitor to study its effects on interleukin-6 (IL-6)-induced loss of forkhead box P3 (Foxp3) gene expression in B-lymphocyte-induced maturation protein 1 (Blimp1)-Treg cells.

Biochem/physiol Actions

SGI-1027 is a DNA methyltransferase (DNMT) inhibitor with IC₅₀ values of 6-13 μM for DNMT3B, DNMT3A and DNMT1. SGI-1027 directly inhibits DNMT activity by competing with the cofactor, S-adenosylmethionine (SAM) in the methylation reaction. SGI-1027 treatment of cancer cell lines induced degradation of DNMT1, but not DNMT3A or DNMT3B, and in RKO cells caused re-expression of the silenced tumor supressor genes p16, MLH1 and TIMP3.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable